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10417-94-4 molecular structure
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(5Z,8Z,11Z,14Z,17Z)-icosa-5,8,11,14,17-pentaenoic acid

ChemBase ID: 45
Molecular Formular: C20H30O2
Molecular Mass: 302.451
Monoisotopic Mass: 302.2245802
SMILES and InChIs

SMILES:
OC(=O)CCC/C=C\C/C=C\C/C=C\C/C=C\C/C=C\CC
Canonical SMILES:
CC/C=C\C/C=C\C/C=C\C/C=C\C/C=C\CCCC(=O)O
InChI:
InChI=1S/C20H30O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20(21)22/h3-4,6-7,9-10,12-13,15-16H,2,5,8,11,14,17-19H2,1H3,(H,21,22)/b4-3-,7-6-,10-9-,13-12-,16-15-
InChIKey:
JAZBEHYOTPTENJ-JLNKQSITSA-N

Cite this record

CBID:45 http://www.chembase.cn/molecule-45.html

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NAMES AND DATABASE IDS

NAMES AND DATABASE IDS

Names Database IDs
IUPAC name
(5Z,8Z,11Z,14Z,17Z)-icosa-5,8,11,14,17-pentaenoic acid
IUPAC Traditional name
icosapent
eicosapentaenoic acid
Synonyms
Eicosapentaenoic acid
EPA
Icosapentaenoic acid
Timnodonic acid
Icosapent
cis-5,8,11,14,17-Eicosapentaenoic acid
(5Z,8Z,11Z,14Z,17Z)-5,8,11,14,17-Eicosapentaenoic Acid
(all-Z)-5,8,11,14,17-Eicosapentaenoic Acid
EPA 45G
Icosapent
Incromega E 7010SR
Ropufa 70
Eicosapentaenoic Acid
二十碳五烯酸
顺式-5,8,11,14,17-二十碳五烯酸
CAS Number
10417-94-4
MDL Number
MFCD00065716
Beilstein Number
1714433
PubChem SID
160963508
46506267
24894640
24894450
24868422
PubChem CID
446284

CALCULATED PROPERTIES

CALCULATED PROPERTIES

JChem ALOGPS 2.1
Acid pKa 4.819772  H Acceptors
H Donor LogD (pH = 5.5) 5.4632735 
LogD (pH = 7.4) 3.6901412  Log P 6.2252493 
Molar Refractivity 101.0706 cm3 Polarizability 36.914207 Å3
Polar Surface Area 37.3 Å2 Rotatable Bonds 13 
Lipinski's Rule of Five false 
Log P 6.53  LOG S -6.02 
Solubility (Water) 2.89e-04 g/l 

PROPERTIES

PROPERTIES

Physical Property Safety Information Pharmacology Properties Product Information Bioassay(PubChem)
Solubility
Chloroform expand Show data source
Ethyl Acetate expand Show data source
Apperance
Colorless Oil expand Show data source
liquid expand Show data source
Melting Point
-54--53 °C(lit.) expand Show data source
Flash Point
199.4 °F expand Show data source
93 °C expand Show data source
Density
0.943 g/mL at 25 °C(lit.) expand Show data source
Refractive Index
n20/D 1.4977(lit.) expand Show data source
Hydrophobicity(logP)
6.1 expand Show data source
Storage Condition
-20°C Freezer expand Show data source
European Hazard Symbols
Corrosive Corrosive (C) expand Show data source
UN Number
3265 expand Show data source
MSDS Link
Download expand Show data source
Download expand Show data source
Download expand Show data source
German water hazard class
3 expand Show data source
Hazard Class
8 expand Show data source
Packing Group
3 expand Show data source
Risk Statements
34 expand Show data source
Safety Statements
26-36/37/39-45 expand Show data source
GHS Pictograms
GHS05 expand Show data source
GHS Signal Word
Danger expand Show data source
GHS Hazard statements
H314 expand Show data source
GHS Precautionary statements
P280-P305 + P351 + P338-P310 expand Show data source
Personal Protective Equipment
Faceshields, full-face respirator (US), Gloves, Goggles, multi-purpose combination respirator cartridge (US), type ABEK (EN14387) respirator filter expand Show data source
RID/ADR
UN 3265 8/PG 3 expand Show data source
Storage Temperature
-20°C expand Show data source
Gene Information
human ... ALOX5(240)mouse ... ALOX5(11689), Pparg(19016)rat ... ALOX5(25290) expand Show data source
mouse ... Pparg(19016) expand Show data source
Purity
≥85% expand Show data source
≥97.0% (GC) expand Show data source
≥98.5% (GC) expand Show data source
≥99% expand Show data source
Grade
analytical standard expand Show data source
purum expand Show data source
Certificate of Analysis
Download expand Show data source
Shelf Life
(limited shelf life, expiry date on the label) expand Show data source
Linear Formula
CH3(CH2CH=CH)5(CH2)3CO2H expand Show data source

DETAILS

DETAILS

DrugBank DrugBank Sigma Aldrich Sigma Aldrich TRC TRC
DrugBank - DB00159 external link
Item Information
Drug Groups approved; nutraceutical
Description Important polyunsaturated fatty acid found in fish oils. It serves as the precursor for the prostaglandin-3 and thromboxane-3 families. A diet rich in eicosapentaenoic acid lowers serum lipid concentration, reduces incidence of cardiovascular disorders, prevents platelet aggregation, and inhibits arachidonic acid conversion into the thromboxane-2 and prostaglandin-2 families. [PubChem]
Indication EPA can be used for lowering elevated triglycerides in those who are hyperglyceridemic. In addition, EPA may play a therapeutic role in patients with cystic fibrosis by reducing disease severity and may play a similar role in type 2 diabetics in slowing the progression of diabetic nephropathy.
Pharmacology Eicosanoids are chemical messengers derived from 20-carbon polyunsaturated fatty acids that play critical roles in immune and inflammatory responses. Both 20-carbon omega-6 fatty acids (arachidonic acid) and 20-carbon omega-3 fatty acids (EPA) can be found in cell membranes. During an inflammatory response, arachidonic acid and EPA are metabolized by enzymes known as cyclooxygenases and lipoxygenases to form eicosanoids. Increasing omega-3 fatty acid intake increases the EPA content of cell membranes and decreases the arachidonic acid content, resulting in higher proportions of eicosanoids derived from EPA. Physiologic responses to arachidonic acid-derived eicosanoids differ from responses to EPA-derived eicosanoids. In general, eicosanoids derived from EPA are less potent inducers of inflammation, blood vessel constriction, and clotting than eicosanoids derived from arachidonic acid.
Affected Organisms
Humans and other mammals
External Links
PDRhealth
Sigma Aldrich - 44865 external link
Biochem/physiol Actions
5-Lipoxygenase inhibitor; reduces thromboxane A2 production.
Sigma Aldrich - 44864 external link
Biochem/physiol Actions
5-Lipoxygenase inhibitor; reduces thromboxane A2 production.
Sigma Aldrich - E2011 external link
Biochem/physiol Actions
5-脂氧合酶抑制剂;减少凝血噁烷 A2 生成。
Sigma Aldrich - E7006 external link
Biochem/physiol Actions
5-脂氧合酶抑制剂;减少凝血噁烷 A2 生成。
包装
5, 10, 25, 50 mg in ampule
Sealed ampule.
Toronto Research Chemicals - E477800 external link
Important polyunsaturated fatty acid of the marine food chain that serves as a precursor for the prostaglandin-3 and thromboxane-3 families. It differs from arachidonic acid (the eicosatetraenoic acid that is a precursor for the prostaglandin and thrombox

REFERENCES

REFERENCES

From Suppliers Google Scholar IconGoogle Scholar PubMed iconPubMed Google Books IconGoogle Books
  • • Bergstrom, S., et al.: J. Biol. Chem., 239, PC 4006 (1964)
  • • Srivastava, K.C., et al.: Biochem. Exp. Biol., 16, 317 (1964)
  • • Kremer, J.M., et al.: Ann. Intern. Med., 106, 497 (1964)
  • • DiGiacomo, R.A., et al.: Am. J. Med., 86, 158 (1964)
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PATENTS

PATENTS

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INTERNET

INTERNET

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